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Dynamic Pricing Strategist – Short-Term Rentals (Canada & USA) Contract or Part-Time • Remote • Expert-Level Role A fast-growing short-term rental management company is seeking an experienced Dynamic Pricing Strategist to lead revenue optimization across a diverse portfolio of properties throughout Canada and the United States. This role requires deep market expertise, the ability to navigate severe seasonal highs and lows, and a proven track record of driving meaningful revenue growth in competitive STR markets. This is a senior specialist position suited only to candidates with top-tier industry experience. About the Role The Dynamic Pricing Strategist will oversee pricing strategy for a wide range of short-term rental accommodations, including luxury homes, resort units, urban apartments, and mid-term rentals. You will analyze market fluctuations, implement pricing rules, forecast demand, and continuously optimize performance based on real-time insights. The ideal candidate has extensive experience working in highly seasonal or volatile markets and understands how to price strategically through unpredictable booking patterns, competition shifts, and demand spikes. Key Responsibilities Develop and execute dynamic pricing strategies across a multi-property STR portfolio in Canada and the U.S. Monitor and adjust pricing based on supply/demand, pacing, regional events, economic indicators, and booking trends. Conduct competitive market analysis using platforms such as PriceLabs, Wheelhouse, Beyond Pricing, KeyData, Airdna, and PMS analytics. Build forecasting models for revenue, occupancy, and pacing trends. Recommend minimum night stays, gap-fill strategies, seasonal adjustments, and rate structures. Provide data-driven insights to leadership and operations teams to support business decisions. Produce weekly or monthly pricing performance reports with clear recommendations. Identify underperforming properties and create strategic plans to increase revenue. Required Experience & Qualifications 5+ years of experience in short-term rental, hotel, or revenue management pricing roles. Demonstrated ability to increase occupancy and ADR in challenging, highly seasonal, or fluctuating markets. Expert-level proficiency with PriceLabs (required). Experience with Beyond, Wheelhouse, or hotel RMS systems is an asset. Strong analytical and modeling skills (Excel/Sheets required). Proven experience managing pricing for large portfolios (50–200+ listings or equivalent). Ability to interpret macro and micro trends, including event-driven demand and regional travel patterns. Exceptional communication skills with the ability to present complex insights clearly. Who You Are Highly analytical and confident in making data-backed decisions. Skilled at identifying pricing opportunities others miss. Comfortable navigating volatile demand patterns across different regions. Detail-oriented, organized, and proactive with recommendations. Able to collaborate clearly with operations, reservations, and leadership teams. Compensation Competitive contractor or part-time compensation based on experience. Performance incentives available. Fully remote and flexible schedule. How to Apply Please submit your resume, portfolio of pricing results, and a brief outline of your experience working with seasonal or volatile STR markets.